Issue 14, 2021

Catalyst-free synthesis of phenanthridines via electrochemical coupling of 2-isocyanobiphenyls and amines

Abstract

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction of in situ formed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode using nBu4NBF4 as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Graphical abstract: Catalyst-free synthesis of phenanthridines via electrochemical coupling of 2-isocyanobiphenyls and amines

Supplementary files

Article information

Article type
Paper
Submitted
15 Jan 2021
Accepted
19 Feb 2021
First published
23 Feb 2021

New J. Chem., 2021,45, 6367-6378

Catalyst-free synthesis of phenanthridines via electrochemical coupling of 2-isocyanobiphenyls and amines

B. K. Malviya, K. Singh, P. K. Jaiswal, M. Karnatak, V. P. Verma, S. S. Badsara and S. Sharma, New J. Chem., 2021, 45, 6367 DOI: 10.1039/D1NJ00250C

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